-
Lucky Ducks Rental Studio
Lucky Ducks Studio is a fully renovated furnished studio in the heart of St. Michaels on Talbot Street in the historic 1850?s McMillian House.Lucky Ducks Studio is a fully renovated furnished studio in the heart of St. Michaels on Talbot Street in the historic 1850?s McMillian House.
Chesapeake Bay Real Estate -Plus LLC-
Chesapeake Bay Real Estate Plus - Dawn Lednum Owner/Broker. The Biggest, Little Office in St. Michaels! We ARE your local realtors. Let us show you what's for sale! You're Going to Love It Here!Chesapeake Bay Real Estate Plus - Dawn Lednum Owner/Broker. The Biggest, Little Office in St. Michaels! We ARE your local realtors. Let us show you what's for sale! You're Going to Love It Here!
Grandview Cottages
Charming cottages and 4 bedroom main house on Broad Creek about 5 miles from town. In-ground pool and waterfront access for crabbing with 14' rowboats for guest use. Available all year.Charming cottages and 4 bedroom main house on Broad Creek about 5 miles from town. In-ground pool and waterfront access for crabbing with 14' rowboats for guest use. Available all year.
Tremezzo Stay
Tremezzo Stay features three luxury vacation rentals located on Maryland's Eastern Shore. Brandon and Marissa have always shared a passion for travel, home renovation, decor - and Italian food! SoTremezzo Stay features three luxury vacation rentals located on Maryland's Eastern Shore. Brandon and Marissa have always shared a passion for travel, home renovation, decor - and Italian food! So
Log Canoe Inn
Waterfront nineteenth-century inn on the St. Michaels Harbor.Waterfront nineteenth-century inn on the St. Michaels Harbor.
Flaneur Vacations
Flaneur’s portfolio includes a diverse range of vacation homes available for discerning travelers looking to join us here on the shore. Each property offers a different experience.Flaneur’s portfolio includes a diverse range of vacation homes available for discerning travelers looking to join us here on the shore. Each property offers a different experience.
Tilghman Island Marina & Rentals
Rent Powerboats, Sailboats, Kayaks, Bikes, Fish/Crab Gear. Kayak our scenic inland water trails or checkout the Bay. Boat operation training/certification. Water tours. Just minutes from St. Michaels.Rent Powerboats, Sailboats, Kayaks, Bikes, Fish/Crab Gear. Kayak our scenic inland water trails or checkout the Bay. Boat operation training/certification. Water tours. Just minutes from St. Michaels.
-
Stay Your Way: Dreamy Stays in St. Michaels & Beyond
Whether you’re planning a romantic retreat, a girls’ getaway, or a solo escape, St. Michaels, Tilghman, and the Bay Hundred area offer a chic and cozy mix of lodging options for every style and budget.
From boutique inns and charming B&Bs to waterfront resorts and private cottage rentals, you’ll find the perfect place to relax, recharge, and wake up to stunning Chesapeake Bay views.
Your dream getaway starts here—book your perfect stay today!
Find the perfect place to fit your needs here.
-
Savor the Flavors of St. Michaels: A Foodie’s Paradise
Nothing says Chesapeake Bay vibes like cracking into a steaming pile of locally caught Maryland blue crabs, but that’s just the beginning! St. Michaels is home to an incredible culinary scene that goes beyond seafood—offering something delicious for every craving.
Seafood & Chesapeake Classics
From perfectly seasoned steamed crabs and golden, lump-filled crab cakes to sweet soft-shell clams and fresh rockfish, our waterfront town is a seafood lover’s dream.A World of Flavor
Craving something else? We’ve got it! St. Michaels serves up an eclectic mix of dining options, including:
Steakhouses for the ultimate indulgence
Authentic Mexican bursting with bold flavors
Classic Italian with homemade pasta & rich sauces
Greek & Mediterranean favorites like gyros, fresh seafood, and vibrant mezze platesFind Your Perfect Spot
Whether you’re looking for a romantic waterfront dinner, a lively crab feast, or a cozy spot for cocktails & small plates, St. Michaels has a table waiting for you. Explore our incredible restaurants here!Find the perfect restaurant here.
-
Shop, Sip & Stroll: A Boutique Lover’s Dream in St. Michaels
Calling all trendsetters, treasure hunters, and boutique lovers—St. Michaels is your ultimate shopping destination! Wander through our charming, walkable streets and explore a carefully curated mix of stylish fashion, artisan jewelry, home décor, and unique finds you won’t see anywhere else.
Chic Boutiques & One-of-a-Kind Finds
From boho-inspired clothing and handcrafted accessories to coastal home décor and locally made art, our shops are full of pieces that tell a story—just like your next adventure.Sip While You Shop
Take a break at one of our local tasting rooms, where you can indulge in small-batch wines, craft cocktails, and gourmet bites—the perfect pairing for a girls’ getaway or a solo shopping spree.Ready to Discover Your Next Favorite Spot?
Explore our unique shops and boutiques right here in St. Michaels—where every corner holds something special. Come shop, sip, and stay a while!Find our unique shops here.
-
Whether you're an experienced kayaker, a day-tripping boater, a sailing novice, a history buff, an avid fisherman, or anyone else who yearns to spend some time on the water, you will find something to do in St. Michaels and Tilghman Island. It's time to get out on the water and enjoy the outdoors! Find your boating options here.
